Molecular dynamic simulation of asphaltene co-aggregation with humic acid during oil spill

Zhu, Xinzhe; Chen, Daoyi; Wu, Guozhong

doi:10.1016/j.chemosphere.2015.06.074

Cited by 45 publications

(55 citation statements)

References 62 publications

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“…The structure of the peat or the low-rank coal can be represented by humic substances (HSs). This facilitates the simulation of element enrichment in coals since candidates of HSs structure are intensively researched in previous studies (Gao et al, 2015;Ramalho et al, 2007;Sviatenko et al, 2016;Zhu et al, 2015). Although the concrete molecular structure of HSs has yet not been determined due to its large molecular size and complexity, the main functional groups able to form complex with metals include carboxyl, hydroxyl, and phenol of local configuration.…”

Section: Introductionmentioning

confidence: 99%

Binding characteristics of Cd²⁺, Zn²⁺, Cu²⁺, and Li⁺ with humic substances: Implication to trace element enrichment in low-rank coals

Xing

Zhang

et al. 2016

Energy Exploration & Exploitation

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Binding characteristics of metal ions (Li + , Cd 2+ , Zn 2+ , Cu 2+ ) with humic substances (HSs) are investigated by first principle calculation at BP86/SDD level. In the present work, HSs are well represented by singly deprotonated alkyl/aryl carboxylic acid. The results reveal that the bidentate is the strongest complexation form. Moreover, with the increase of ionic potential, the binding energies of HSs to chelate metal ions increase in order, Li + < Cd 2+ < Zn 2+ < Cu 2+ . The nature of the ligand also exerts important influence on the stability of organometallic complexes. Specifically, for Li + , the ionic bond-forming part occurs as electroneutrality. Whatever electrondonating groups or electron-withdrawing groups including alkyl, aryl and its derivatives (salicylic acid and m (p)-substituted gallic acid by hydroxyl or amino) and carbon-carbon double bond connects to the carboxylate group, the electron density of the ionic bond-forming part will be changed resulting in the decrease of binding energy (BE). However, for ions with high ionic potential or high positive charge density (Cd 2+ , Cu 2+ and Zn 2+ ), the ionic bond-forming part is positively charged. From electron-withdrawing groups to electron-donating groups, the extent to deviate from electroneutrality is gradually decreased, although the quantity of electron is possibly insufficient to balance the extra positive charge. As a result, the BE value gradually increases, but does not reach a maximum for studied ions and ligands. Besides, mixed functional groups are able to stabilize organometallic complexes. The optimal mixed functional group is carboxyl and hydroxyl on ortho position, followed by two hydroxyls, hydroxyl and carbonyl, carboxyl and carbonyl, In the end, the geochemical behavior of trace elements in coalification is predicted: small organic acids generated by decomposition of dead plants in relatively oxidized environments will facilitate the enrichment of lithium and this proportion of lithium will be released into pore water in the polymerization of small molecules, possibly accumulating in secondary minerals in low-rank coals; metal ions with high ionic potential bonded by organic molecules will be released in a later stage and accumulate in slightly higher rank coals.

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Section: Introductionmentioning

confidence: 99%

Binding characteristics of Cd²⁺, Zn²⁺, Cu²⁺, and Li⁺ with humic substances: Implication to trace element enrichment in low-rank coals

Xing

Zhang

et al. 2016

Energy Exploration & Exploitation

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“…Previous studies demonstrated that the properties of pore water in the Na-MMT with interlayer space smaller than 2.5 nm differed significantly with that of bulk water (Karaborni et al, 1996). A comparison with Zhu et al (2015) showed that the diffusion coefficient of asphaltenes in the 2.5 nm water-filled MMT interlayer was one-order of magnitude lower than that in bulk water (1e4.5 Â 10 À10 m 2 s À1 ). Fig.…”

Section: Resultsmentioning

confidence: 90%

“…The LHA sample was purchased from the International Humic Substance Society, while the asphaltene samples were extracted from the Athabasca oil sands using the methods elaborated by Zhu et al (2015). Stock solutions were made up by dissolving asphaltenes in toluene (1000 mg L À1 ) and LHA in DMSO (250, 500, 1000 mg L À1 ), which were sampled with the volume ratio of 1:1 to make up mixture samples.…”

Section: Afm Testmentioning

confidence: 99%

“…Equilibration and MD simulation were performed for each simulation system using the procedures described by Zhu et al (2015). Briefly, energy minimization was run using the steepest descent algorithm with the convergence level of 1000 kJ (mol nm) À1 .…”

Section: Molecular Dynamic Simulationmentioning

confidence: 99%

“…Our recent study demonstrated that the presence of humic substances increased the adsorption of asphaltenes on quartz surface and tend to promote asphaltene aggregation . Zhu et al (2015) further reported the co-aggregation of asphaltenes and humic acids at the oil-water interface and in the bulk water, respectively, using MD simulation. Insights were gained into the interactions between asphaltenes and humic substances during the transport of asphaltenes from the spilled oil to the water.…”

Section: Introductionmentioning

confidence: 96%

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Insights into asphaltene aggregation in the Na-montmorillonite interlayer

Zhu

Chen

2016

Chemosphere

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Density functional theory investigation of the contributions of π-π stacking and hydrogen bonding with water to the supramolecular aggregation interactions of model asphaltene heterocyclic compounds

Lessa,

Stoyanov,

de Carneiro

et al. 2024

J Mol Model

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Context A complex supramolecular process involving electrostatic and dispersion interactions and asphaltene aggregation is associated with detrimental petroleum deposition and scaling that pose challenges to petroleum recovery, transportation, and upgrading. The homodimers of seven heterocyclic model compounds, representative of moieties commonly found in asphaltene structures, were studied: pyridine, thiophene, furan, isoquinoline, pyrazine, thiazole, and 1,3-oxazole. The contributions of hydrogen bonding involving water bridges spanning between dimers and π-π stacking to the total interaction energy were calculated and analyzed. The distance between the planes of the aromatic rings is correlated with the π-π stacking interaction strength. All the dimerization reactions were exothermic, although not spontaneous. This was mostly modulated by the strength of the hydrogen bond of the water bridge and the π-π stacking interaction. Dimers bridged by two water molecules were more stable than those with additional water molecules or without any water molecule in the bridge. Energy decomposition analysis showed that the electrostatic and polarization components were the main stabilizing terms for the hydrogen bond interaction in the bridge, contributing at least 80% of the interaction energy in all dimers. The non-covalent interaction analysis confirmed the molecular sites that had the strongest (hydrogen bond) and weak (π-π stacking) attractive interactions. They were concentrated in the water bridge and in the plane between the aromatic rings, respectively. Methods The density functional ωB97X-D with a dispersion correction and the Def2-SVP basis set were employed to investigate supramolecular aggregates incorporating heterocycles dimers with 0, 1, 2, and 3 water molecules forming a stabilizing bridge connecting the monomers. The non-covalent interactions were analyzed using the NCIplot software and plotted as isosurface maps using Visual Molecular Dynamics.

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Molecular dynamic simulation of asphaltene co-aggregation with humic acid during oil spill

Cited by 45 publications

References 62 publications

Binding characteristics of Cd²⁺, Zn²⁺, Cu²⁺, and Li⁺ with humic substances: Implication to trace element enrichment in low-rank coals

Binding characteristics of Cd²⁺, Zn²⁺, Cu²⁺, and Li⁺ with humic substances: Implication to trace element enrichment in low-rank coals

Insights into asphaltene aggregation in the Na-montmorillonite interlayer

Density functional theory investigation of the contributions of π-π stacking and hydrogen bonding with water to the supramolecular aggregation interactions of model asphaltene heterocyclic compounds

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Molecular dynamic simulation of asphaltene co-aggregation with humic acid during oil spill

Cited by 45 publications

References 62 publications

Binding characteristics of Cd2+, Zn2+, Cu2+, and Li+ with humic substances: Implication to trace element enrichment in low-rank coals

Binding characteristics of Cd2+, Zn2+, Cu2+, and Li+ with humic substances: Implication to trace element enrichment in low-rank coals

Insights into asphaltene aggregation in the Na-montmorillonite interlayer

Density functional theory investigation of the contributions of π-π stacking and hydrogen bonding with water to the supramolecular aggregation interactions of model asphaltene heterocyclic compounds

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Binding characteristics of Cd²⁺, Zn²⁺, Cu²⁺, and Li⁺ with humic substances: Implication to trace element enrichment in low-rank coals

Binding characteristics of Cd²⁺, Zn²⁺, Cu²⁺, and Li⁺ with humic substances: Implication to trace element enrichment in low-rank coals